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Vacation rentals with a pool in Guardistallo

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Guardistallo

  • Total vacation rentals

    Explore 130 vacation rentals in Guardistallo

  • Nightly prices starting at

    Guardistallo vacation rentals start at ﺩ.ﺇ 220 per night before taxes and fees

  • Verified guest reviews

    Over 840 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 90 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Guardistallo vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Guardistallo rentals

  • 4.6 Average rating

    Guardistallo stays receive an average rating of 4.6 out of 5 from guests

Top-rated rentals with a pool in Guardistallo

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite
Bungalow in Riparbella
4.93 out of 5 average rating, 41 reviews

Superior Lodge with 2 bedrooms and outdoor tub

An open air holiday in a comfortable solution: first bedroom with 1 bunk bed and a single bed, and a second one with a double bed; bathroom with shower, hairdryer, linen and courtesy kit. Living room with equipped kitchenette, small fridge and veranda. Our tents are located in a panoramic position, and is possible to enjoy the pools in our Resort - seasonal opening. Easily accessible by car, with a big and free of cost parking; outdoor tub for exclusive use, air conditioning, TV and free wi-fi. 

Top guest favorite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 343 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.

Superhost
A unique treehouse is highlighted among vibrant green grass adorned with clusters of purple flowers. Towering trees provide shade, and the structure features a deck that overlooks the surrounding natural landscape, inviting a sense of tranquility and harmony with nature.
Home in Galluzzo
4.88 out of 5 average rating, 817 reviews

TREEhouse/casaBARTHEL

casaBARTHEL is a perfect place for a vacation and an artist residency, immersed in the Tuscan landscape only 15' from the florentine Duomo. Come and live with us; enjoy the olive trees, the kitchen garden, our horse Astro and our family life style, away from the working rhythm. By providing wifi only in the communal courtyard we suggest to take a break from been connected with elsewhere and enjoy the 'here and now' . But if you need to work you can rent a portable private connection from us.

Guest favorite
Home in Montescudaio
4.96 out of 5 average rating, 131 reviews

Open space immerso nella natura

Casa namaste è un piccolo casolare in pietra con interni curatissimi a 1 km dal borgo medievale di Montescudaio La casa è completamente circondata da bosco e querce secolari a 150 metri scorre il fiume Cecina nel giardino di 5000 metri quadrati c'è una sorgente naturale con una grande vasca in pietra per rinfrescarsi e una doccia calda esterna immersa nel verde..abbiamo una linea adsl Vodafone con download 33 e upload 1.4..da questa primavera è inoltre disponibile smart TV e climatizzatore

Guest favorite
Cottage in Castellina in Chianti
4.97 out of 5 average rating, 112 reviews

Cottage Cappero - Masseto In Chianti

MASSETO IN CHIANTI è un villaggio privato dove potrete rilassarvi nel vostro giardino privato e in piscina, fare sport, o utilizzare come base per visitare città rinascimentali: Firenze, Siena, San Gimignano, Arezzo, Volterra. Offriamo altri tre cottage con accesso indipendente e giardinetto privato: Quinto (2 letti), Vittoria (4 letti), Leccio (6 letti). La piscina è condivisa dai 4 cottage, ciascuno dispone di un gazebo privato, con distanze garantite e sanificazione a norma Covid-19.

Top guest favorite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa in Montecatini Val di Cecina
4.99 out of 5 average rating, 137 reviews

Torre dei Belforti

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Top guest favorite
A spacious outdoor pool surrounded by deck chairs offers a serene view of the countryside. Thatched umbrellas provide shade, while the warm hues of sunset illuminate the rustic buildings in the background, emphasizing the tranquility of the setting.
Apartment in Santa Luce
4.93 out of 5 average rating, 59 reviews

Michelangelo apt ~ wild Tuscany Hills ~ Le Fraine

Take a break in the wild Tuscan hills, just 15 km from the sea. Agriturismo Le Fraine offers its guests 4 apartments and a large park with a pool overlooking the vineyards. The Michelangelo apartment is the perfect solution for a holiday to enjoy with your loved ones. It features two bedrooms (1 double bed - 2 single beds), a bathroom with a shower, a living room with a kitchen, and a sofa bed. From the private veranda, let your gaze wander over the hills and vineyards.

Guest favorite
The eco-friendly swimming pool reflects the rustic cottage and surrounding greenery under a clear blue sky. Smooth pebbles line the shallow area of the pool, creating a natural aesthetic. Tall cypress trees and a vibrant umbrella are visible, integrating seamlessly with the tranquil landscape.
Apartment in Guardistallo
5 out of 5 average rating, 15 reviews

Agriturismo Ai Massi Annamaria (trilocale 57mq)

Appartamento (trilocale di 57 mq, per un totale di 4 posti letto) vista mare, situato al SECONDO PIANO del casolare, ingresso sul lato ovest. Dispone di cucina (dotata frigorifero, lavastoviglie, fornelli ad induzione, forno a microonde, bollitore, tostapane, frullatore ad immersione e Moka) soggiorno (tv e wifi), due camere da letto con letto matrimoniale e bagno. La struttura dispone di piscina ecocompatibile ed affaccia sulle campagne della Costa degli Etruschi.

Top guest favorite
A terrace overlooking the coastline is equipped with a large umbrella, sun loungers, and a small pool. The rocky coastline and clear blue water are visible, while lush greenery frames the outdoor area, creating a serene environment for relaxation.
Home in Rosignano Marittimo
4.95 out of 5 average rating, 107 reviews

Casa Frontemare con accesso al mare esclusivo

Casa Frontemare è una proprietà completamente ristrutturata con accesso diretto al mare, dalla quale è possibile godere di una vista panoramica sul mare, sulle isole toscane e di meravigliosi tramonti. E' un luogo perfetto per gli amanti di una vacanza all'insegna del relax e della privacy. La vicinanza alle città d'arte toscane e ai piccoli borghi tipici fa si che sia possibile anche andare alla scoperta di nuovi luoghi e scoprire i sapori della cucina italiana.

Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 102 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Top guest favorite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home in Montaione
4.96 out of 5 average rating, 140 reviews

Cercis - La Palmierina

E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Top guest favorite
Vacation home in Lajatico
5 out of 5 average rating, 38 reviews

Rosa: Tuscan Views & Pool, Walk to Town

Welcome to La Lunaria di Lajatico, an elegant residence in the Tuscan hills, just a 7-minute walk from the village of Lajatico, hometown of Andrea Bocelli. With two pools, panoramic terraces overlooking rolling hills, olive groves, BBQ, and full modern comfort, it offers four rustic-chic apartments—ideal for families, couples, or groups seeking authentic Tuscany close to town.

Popular amenities for Guardistallo rentals with a pool

When is the best time to visit Guardistallo?

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Avg. priceﺩ.ﺇ 782ﺩ.ﺇ 657ﺩ.ﺇ 584ﺩ.ﺇ 595ﺩ.ﺇ 566ﺩ.ﺇ 580ﺩ.ﺇ 694ﺩ.ﺇ 823ﺩ.ﺇ 569ﺩ.ﺇ 617ﺩ.ﺇ 643ﺩ.ﺇ 782
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